Urea → (2-Bromophenylsulphonyl)nitromethane

Nitromethane (4.6 ml, 82.3 mmol) was added to a stirred solution of sodium hydroxide (7.9 g, 197.5 mmol) in water (50 ml). A solution of sodium 2-bromobenzenesulphinate (20 g, 82.5 mmol) in water (100 ml) was added, followed by dichloromethane (50 ml). The reaction mixture was cooled in an ice bath and a solution of potassium ferricyanide (3 g, 9.1 mmol) in water (20 ml) was added, followed by solid sodium persulphate (12 g, 50.4 mmol). The resultant deep orange solution was allowed to stir for one hour at ambient temperature. Ether (25 ml) was added, followed by urea (5 g), and the pH of the reaction mixture was then adjusted to pH 6 with 20% aqueous acetic acid solution. The organic phase was separated and the aqueous phase was extracted with ether (150 ml×bb 3). The combined organic phases were dried (MgSO4), and the solvent was removed by evaporation. The resultant brown solid was purified by MPLC, eluting with dichloromethane, to give (2-bromophenylsulphonyl)nitromethane as a pale yellow solid (0.197 g), m.p. 74°-76° C.; microanalysis, found: C,29.7; H,2.1; N,4.9%; C7H6BrNO4S requires: C,30.0; H,2.1; N,5.0%.

1. temperatureThe reaction mixture was cooled in an ice bath
2. customThe organic phase was separated
3. extractionthe aqueous phase was extracted with ether (150 ml×bb 3)
4. dry with materialThe combined organic phases were dried (MgSO4)
5. customthe solvent was removed by evaporation
6. customThe resultant brown solid was purified by MPLC
7. washeluting with dichloromethane

ORDレコード

ord-2c79672df78a4af4b6b298dbf09a0a64

出典データセット

uspto-grants-1992_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05153227